If you could live your financial life again, what would you do differently?

Rent my house in California and not sell it.

Rent in a neighborhood that I wanted to live in before I could afford to buy there, rather than buy in a lesser neighborhood just to own a home (whose value when I sold it ended up being about the same as just renting it).

I made all the classic mistakes, and also didn’t have access to after tax 401k/IRA. If I did it over again:

1. max out ROTH 401k and/or ROTH IRA contributions.
2. manage IRA contributions so that I could do a mega backdoor ROTH conversion at some point.
3. Except for maxing out the employee stock purchase plan (which I did and it worked very well), don’t buy individual stocks (I lost 50% in the Dot Bomb collapse) – invest only in index funds and manage the entire portfolio (a Lazy Portfolio at that) to a single asset allocation, set to 80/20 (back when I was in my 30s-40s).

I would have invested in low-cost index funds, instead of purchasing GE stock through employer. I would have paid taxes on contributions to 401K. I would fully maximize 401k Roth opportunities! I would have been a little more aggressive in stock allocation versus bonds.

When I was a younger worker just learning about investing, I bought stocks instead of index funds. I would have also paid greater attention to asset location between my pre-tax and taxable accounts.

I would have taken my own advice and not traded my accounts as much

I would confront my now ex-wife about the dramatic change in her spending habits and lack of discipline.

Listened to my gut more when I was in my mid to late twenties. I finally began to make a good living and rather than live frugally I bought a house and a new car. If I had lived like a student for even 5 years while I was still single I could have made some more substantial investments.

Never carry credit card debt. Haven’t in many years, but didn’t figure this out early enough.

Instead of starting drawing social security at age 62, I would have waited until I turned 70.

I am a conservative investor but I do wish that in my younger years that my portfolio was more heavily weighted towards stocks.

I would have been a bit more aggressive with investments. And I would have used Roth accounts as soon as they were available.

I would save more and learn about stock market investing earlier. We spent too much on mutual fund fees and taxes when we could have been buying stocks.